Intermediate isocyana to benzenesulfonamide compounds

ABSTRACT

Compounds having the formula:  &lt;IMAGE&gt;  wherein X is C1-C4 alkyl, C1-C8 alkoxy or halogen; Y is hydrogen, halogen, or C1-C4 dialkylamino; R1 is C1-C8 straight chain or branched alkyl, C3-C8 cycloalkyl, C3-C8 alkenyl or C3-C8 alkoxy; R2 is C1-C8 straight chain or branched alkyl, C3-C8 alkenyl, C3-C8 cycloalkyl, halo substituted C3-C8 alkenyl, C3-C8 alkynyl, C1-C4 alkoxy, cyano C1-C4 alkyl, alkoxyalkyl, phenyl, aralkyl, C1-C4 acyl, C1-C4 carbalkoxyalkyl, C1-C4 carbalkoxyalkyl substituted by C1-C4 alkyl, phenylmethyl or methylthioethyl, dialkylaminoethyl, or tetrahydrofuranylmethyl; R1 and R2 taken together form a C3-C8 membered heterocyclic ring containing one or more heteroatoms. The compounds are useful as intermediates for making herbicides.

This is a division of application Sr. No. 07/742,957 filed Aug. 9, 1991,now U.S. Pat. No. 5,169,430.

FIELD OF THE INVENTION

This invention relates to a class of compounds, i.e., benzenesulfonamidederivatives, having substituted thereon a pyrimidinyl moiety, whichcompounds exhibit desirable pre- and post-emergent herbicidal activity.In other aspects, this invention relates to herbicidal compositionsincorporating such compounds and to a method of controlling the growthof undesirable plants, such as weeds. In further aspects, this inventionrelates to novel intermediates useful for the production of the novelherbicides and to processes for producing such compounds.

BACKGROUND OF THE INVENTION

Weeds compete with crops for light, moisture, nutrients and space andconsequently inhibit the production of foliage, fruit or seed ofagricultural crops. The presence of weeds may also reduce the quality ofthe harvested crop and reduce harvesting efficiency. Weed control isessential for maximum production of many agronomic and horticulturalcrops including corn, (Zea mays L.), cotton (Gossypium SP), sunflower(Helianthus annus L.) and soybeans (Glycine max (L.) Merr.). Weeds onnon-cropped areas may cause a fire hazard, undesirable drifting of sandor snow, or irritation to persons with allergies. Consequently, it isdesirable to suppress growth of unwanted weeds.

While a large number of compounds exhibiting herbicidal activity areknown, it is nonetheless advantageous to obtain additional compoundswhich effectively control the growth of unwanted vegetation.

DESCRIPTION OF RELATED ART

U.S. Pat. No. 4,859,229 to Wenger discloses certain substituted3-aryluracils having an ether (thio)carbamyloxy or sulphamyloxysubstituent on the aromatic moiety, and weed control compositions basedthereon. Compounds according to the present invention have differentstructures and effect greater selectivity to certain crops.

Lutz and Trotto in J. Heterocyclic Chemistry, (1972), 9, (3), 513discuss means of synthesizing 6-(trifluoromethyl) cytosines and6-(trifluoromethyl) uracils. It will become apparent that the compoundsand processes disclosed in the above references differ significantlyfrom those herein disclosed.

SUMMARY OF THE INVENTION

In one aspect, this invention relates to compounds of formula I below:##STR2## wherein: R is hydrogen, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, formyl,C₂ -C₆ alkanoyl, C₃ -C₄ alkenyl or C₃ -C₄ alkynyl, or alkali metal;

X is C₁ -C₄ alkyl, C₁ -C₈ alkoxy, cyano, or halogen;

Y is hydrogen, halogen, or C₁ -C₄ dialkylamino;

R¹ is hydrogen, C₁ -C₈ straight chain or branched alkyl, C₃ -C₈cycloalkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkoxy or C₃ -C₈ hydroxyalkyl;

R² is hydrogen, C₁ -C₈ straight chain or branched alkyl, C₃ -C₈ alkenyl,C₃ -C₈ cycloalkyl, halo substituted C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁-C₄ alkoxy, hydroxy C₁ -C₄ alkyl, cyano C₁ -C₄ alkyl, 2,3-epoxypropyl,2,2-dialkoxyethyl, alkoxyalkyl, phenyl, aralkyl, C₁ -C₄ acyl, C₁ -C₄carbalkoxyalkyl, C₁ -C₄ carbalkoxyalkyl substituted by C₁ -C₄ alkyl,phenylmethyl or methylthioethyl, (1,3-dioxolan-2-yl) alkyl,dialkylaminoethyl, or tetrahydrofuranylmethyl;

R³ is hydrogen, halogen or C₁ -C₄ alkyl;

R⁴ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl

R¹ and R² taken together form a C₃ -C₈ membered heterocyclic ringcontaining one or more heteroatoms; as well as salts of the compounds offormula I in which R is hydrogen or R¹ is hydrogen.

In another aspect, this invention relates to an herbicidal compositioncomprising:

(a) a compound having the structure of formula (I) above; and

(b) a suitable carrier:

In yet another aspect of the present invention, a process (hereinafterreferred to as "process A") for preparing the above-described class ofcompounds having the structural formula I is described. In the processof forming the above described class of compounds, with the proviso thatR is an alkali metal, a compound having the structural formula ##STR3##where R³ is hydrogen or C₁ -C₄ alkyl; R⁴ is C₁ -C₄ alkyl or C₁ -C₄haloalkyl; and R⁵ is C₁ -C₆ alkyl, is reacted with sodium hydride. Theproduct of this reaction is further reacted with a novelisocyanatobenzenesulfonamide having the structural formula: ##STR4##where X and Y have the meanings given above for the compound of thisinvention and with the proviso that R¹ and R² cannot be hydrogen. Theproduct of formula I, where R is an alkali metal, may be isolated orfurther reacted to produce other compounds of formula I.

Additional compounds in accordance with this invention where R is C₁ -C₄alkyl, C₃ -C₄ alkenyl, C₁ -C₄ haloalkyl, or C₃ -C₄ alkynyl, are made byreacting a precursor compound of the present invention where R. is analkali metal, with an alkylating agent, R-Z, where R has the meaningsdefined above and Z represents a leaving group.

In further accordance with the process of making the compounds of thisinvention, a compound in which R is hydrogen is prepared by reacting aprecursor compound of the present invention wherein R is an alkalimetal, with a strong acid.

The novel isocyanatobenzenesulfonamide .. intermediate is prepared byphosgenation of the amino-substituted benzenesulfonamide.

Another process (hereinafter referred to as "process B") for preparingthe above described class of compounds having the structural formula Ifirst involves the chlorosulfonation of certain 3-aryl substituted2,4-(1H,3H)-pyrimidinediones having the structural formula ##STR5##where R, R³, R⁴, X and Y have the meanings given above with the provisothat R is not alkali metal, formyl, alkanoyl, alkenyl or alkynyl, toproduce novel pyrimidinyl substituted benzenesulfonyl chlorideintermediates of the structural formula ##STR6## The pyrimidinylsubstituted benzenesulfonyl chloride is then reacted with an appropriateamine to produce compounds of formula I.

In still further accordance with the instant invention another process(hereinafter referred to as "process C") for making the aforesaidcompounds is carried out by reacting certain substitutedpyrimidinylbenzenesulfonamides with an alkyl halide in the presence ofsodium hydride in N, N-dimethylformamide or other suitable solvents.

In yet still further accordance with a process of making certaincompounds of formula I (hereinafter referred to as process D), theproducts of process C may be hydrogenated over a palladium/carboncatalyst.

It has been found that certain of the aforedescribed[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides possessexcellent herbicidal properties. These properties are surprisinglyeffective in both pre- and post-emergent applications. That is, theclass of compounds of the present invention effectively controlsundesired vegetation both prior to and after emergence from soil.

In still another aspect of the present invention, a method forcontrolling weeds and other undesirable vegetation is disclosed. In thismethod, an herbicidally effective amount of a compound having thestructural formula I is applied to the locus to be protected along witha suitable carrier.

DETAILED DESCRIPTION OF THE INVENTION.

The compositions of this invention contain compounds having thestructural formula (I) shown below: ##STR7## wherein: R is hydrogen, C₁-C₄ alkyl, C₁ -C₄ haloalkyl, formyl, C₂ -C₆ alkanoyl, C₃ -C₄ alkenyl orC₃ -C₄ alkynyl, or alkali metal;

X is C₁ -C₄ alkyl, C₁ -C₈ alkoxy, cyano, or halogen;

Y is hydrogen, halogen, or C₁ -C₄ dialkylamino;

R¹ is hydrogen, C₁ -C₈ straight chain or branched alkyl, C₃ -C₈cycloalkyl, C₃ -C₈ alkenyl, C₃ -C₈ alkoxy or C₃ -C₈ hydroxyalkyl;

R² is hydrogen, C₁ -C₈ straight chain or branched alkyl, C₃ -C₈ alkenyl,C₃ -C₈ cycloalkyl, halo substituted C₃ -C₈ alkenyl, C₃ -C₈ alkynyl, C₁-C₄ alkoxy, hydroxy C₁ -C₄ alkyl, cyano C₁ -C₄ alkyl, 2,3-epoxypropyl,2,2-dialkoxyethyl, alkoxyalkyl, phenyl, aralkyl, C₁ -C₄ acyl, C₁ -C₄carbalkoxalkyl, C₁ -C₄ carbalkoxyalkyl substituted by C₁ -C₄ alkyl,phenylmethyl or methylthioethyl, (1,3-dioxolan-2-yl)alkyl,dialkylaminoethyl, or tetrahydrofuranylmethyl;

R³ is hydrogen, halogen or C₁ -C₄ alkyl;

R⁴ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl

R¹ and R² taken together form a C₁ -C₄ membered heterocyclic ringcontaining one or more heteroatoms; as well as salts of the compounds offormula I in which R is hydrogen or R¹ is hydrogen.

Preferably, compounds according to the present invention have thestructural formula I wherein R is C₁ -C₃ alkyl or C₁ -C₄ alkynyl; X ishalogen or C₁ -C₄ alkyl; Y is halogen or hydrogen; R¹ is hydrogen or C₁-C₃ alkyl or C₃ -C₈ hydroxyalkyl; R² is C₁ -C₃ alkyl, C₃ -C₈ cycloalkyl,C₃ -C₄ alkenyl, alkoxylalkyl, aralkyl, hydroxy C₁ -C₄ alkyl or2,3-epoxypropyl, R³ is hydrogen, and R⁴ is trifluoromethyl

Still more preferably, compounds according to the present invention havestructural formula I wherein R is methyl; X is chlorine or fluorine; Yis fluorine or hydrogen; R¹ is hydrogen, methyl, or C₁ -C₄hydroxylalkyl; R² is hydrogen, C₁ -C₄ alkyl, C₃ -C₆ cycloalkyl, C₁ -C₄alkoxy, alkoxyalkyl, hydroxy C₁ -C₄ alkyl, cyanoalkyl,2,2-dialkoxyethyl, carbalkoxyalkyl, R³ is hydrogen; and R⁴ istrifluoromethyl.

Most preferably, compounds according to the instant invention have thestructural formula I wherein R is methyl X is chlorine Y is hydrogen orfluorine; R¹ is methyl, ethyl, or hydrogen; R² is methyl, ethyl,methoxy, hydroxyethyl, acetyl, methoxyethyl, 2,2-dimethoxyethyl,1-carbethoxyethyl, or 1-carbethoxy-2-methylpropyl; R³ is hydrogen; andR⁴ is trifluoromethyl.

The present invention is also directed to a composition having utilityas an herbicidal agent which comprises a compound having the structuralformula I and a suitable carrier therefor.

Preferably, compositions of the present invention comprise a compoundhaving the structural formula I in which R, X, Y, R¹ and R² incorporatethe embodiments indicated in the above described preferable compoundsand a suitable carrier therefor.

Still more preferably, compositions of the present invention comprise acompound having the structural formula I where R, X, Y, R¹ and R²incorporate the embodiments disclosed for the above described still morepreferable compounds and a suitable carrier therefor.

Most preferably, compositions of the present invention comprise acompound having the structural formula I where R, X, Y, R¹ and R²incorporate the embodiments disclosed for the above described mostpreferable compounds and a suitable carrier therefor.

The principal utility of the compositions of the present application areas herbicides and are made of:

(a) an herbicidally effective amount of a novelpyrimidylbenzenesulfonamide compound according to the present inventionand

(b) a suitable carrier.

Such compositions may comprise one or more of the novelpyrimidinylbenzenesulfonamides of this invention. To prepare suchagriculturally useful compositions, the active ingredient(s) may bemixed with an adjuvant to provide compositions in the form offinely-divided particulate solids, granules, pellets, wettable powders,flowable liquids, soluble powders, solutions, and aqueous or organicsolvent dispersions or emulsions. Such formulations may be of severaldifferent physical and chemical types which can be made by one withordinary skill in the art. For instance, the agriculturally activecompound may be impregnated on finely-divided or granular inorganic ororganic carriers such as appapulgite clay, sand., vermiculite, corn cob,activated carbon or other granular carriers known to the art. Theimpregnated granules may then be spread on, or incorporated into thesoil.

Alternatively, the active ingredient(s) may be formulated as a wettablepowder by grinding into a fine powder and mixing with an inactivepowdered carrier to which a surface active dispersing agent has beenadded. Typical powdered solid carriers are the various mineral silicates(such as mica, talc, pyrophyllite, clays and the like) or powderedorganic materials (e.g., corn cob). The wettable powder may then bedispersed in water and sprayed on the soil surface, or on crop or weedplants.

Similarly, an emulsifiable concentrate may be prepared by dissolving theactive ingredient(s) in a solvent such as naphtha, toluene, or otheraromatic or aliphatic hydrocarbon to which a surface active dispersingagent generally has been added. The emulsifiable concentrate may then bedispersed in water and applied by spraying.

The concentration of active ingredient(s) in the composition may varywidely, typically ranging from about 1% to about 95% by weight. Theconcentration of active ingredient(s) in dispersions applied to the soilor foliage is typically between about 0.002% and about 80% by weight.

Formulations containing the active ingredient(s) may be dispersed inwater or an organic liquid (such as oil) and applied to target plants.Surface active agents may be added to the solution to be applied toincrease its qualitative or quantitative range of activity. Suitablesurface active agents are well known to those skilled in the art.Reference may be made to McCutcheon's Detergents and Emulsifiers (1980,Allured Publ. Co., Ridgewood, N.J.) for examples of appropriate surfaceactive agents. Similarly, such formulation may be applied to the soileither as a liquid or a granule.

In preemergence herbicidal applications, the compound of this inventionis typically applied at a rate from about 0.01 to about 10 pounds peracre (about 0.01 to about 11 kg/ha) to soil which contains weed and cropseed. Such application is made either to the surface of the soil or intothe upper one to three inches (2.5 to 7.5 cm.) of soil. When employed asa postemergence herbicide, the compound is typically applied at a rateof from about 0.01 to about 10 pounds per acre (about 0.01 to about 11kg/ha) to the aerial portions of weeds.

The most suitable rate of application in any given case depends on suchfactors which include the plant species, the stage of plant development,the method of application, the specific biological effect desired, theair and soil temperature, soil type, soil pH, soil fertility, moisture,organic matter content, the condition and vigor of the target plants,the relative humidity and wind velocity of the air around the crop atthe time of treatment, the extent and density of the foliar canopy ofthe target plant, the quantity and intensity of rainfall before andafter treatment, light intensity and light duration per day. All ofthese factors can have an influence on the efficacy of the chemicals fora given weed control use. However, one skilled in the art can, byroutine experimentation, readily determine optimum conditions foremployment of any of the particular pyrimidinyl benzenesulfonamidecompounds of this invention.

The herbicidal use may include control of vegetation at industrial sitesor selective weed control in crop fields.

The following examples are intended to further illustrate the inventionand are not intended to .limit the scope of the invention in any manner.

The first set of examples (A-1 through A-6) are illustrative of processA for producing[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides by reactingan amino substituted benzenesulfonamide with excess phosgene in ethylacetate to form an isocyanatobenzenesulfonamide intermediate, which isin turn reacted with an ester compound, e.g.,ethyl-3-amino-4,4,4-trifluoro-2-butenoate in the presence of sodiumhydride and then subsequently reacted with an acid to yield compounds offormula I where R is hydrogen. Suitable acids include mineral acids suchas hydrochloric acid and sulfuric acid Substituents R¹, R², R³, R⁴, R⁵,X, Y and Z all have the meanings indicated above with the proviso thatR¹ and R² are not hydrogen. Examples A-1 through A-3 depict knowncompounds which are used to make the novel products of Examples A-4through A-6.

Products of the above reaction may, in turn, be reacted with alkylatingcompounds designated R-Z in basic conditions to yield further compoundsof formula I. R has the meanings designated above and Z is a leavinggroup which may include, e.g., halogens, alkylsulfonates orarylsulfonates.

The general reaction scheme for process A is depicted below: ##STR8##

The second set of examples (B-1 through B-7) are illustrative of processB for producing[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides bychlorosulfonation of certain aryl substituted pyrimidinediones to formpyrimidinylbenzenesulfonyl chloride intermediates which are then reactedwith an amine. Chlorosulfonation may be accomplished with.chlorosulfonic acid. Substituent groups in this set of examples, namely,R¹, R², R³, R⁴, R⁵, X, Y and Z, all have the meanings given above. Ifboth X and Y are fluorine, the compounds of this reaction may be furtherreacted with an amine to form products wherein ##STR9##

The reaction scheme for process B is generally depicted below: ##STR10##

The third set of examples (C-1 and C-2) are illustrative of process Cfor producing[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides by reactingcertain substituted pyrimidinylbenzenesulfonamides with an alkyl halidein the presence of sodium hydride in N,N-dimethylformamide. The reactionscheme for process C is generally depicted below: ##STR11##

The fourth example (D-1) is illustrative of process D for producing[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides. In thisprocess, the products of process C or certain other compounds of formulaI may be hydrogenated over palladium/carbon catalyst. The reactionscheme for process D is generally depicted below: ##STR12##

The fifth set of examples (Example V) illustrates the effectiveness ofcertain compounds of this invention as a preemergence herbicide.

The sixth set of examples (Example VI) illustrates the effectiveness ofcertain compounds of this invention as a postemergence herbicide.

I. Preparation of [3,6-dihydro-2,6-dioxo- (2H)pyrimidinyl]benzenesulfonamides by Process A EXAMPLE 1

Preparation of 2-chloro-5-nitrobenzenesulfonylchloride.

To a mixture of 104 g of commercially available sodium2-chloro-5-nitrobenzenesulfonate, 200 ml of acetonitrile and 200 ml ofsulfolane stirred at 25° C., was added 153 ml of phosphorus oxychlorideover a period of 30 minutes. The temperature was not allowed to exceed40° C. After completion of the addition, the reaction mixture was heatedto 70° C. for 1.5 hours. On cooling to 0° C., the reaction mixture waspoured over ice. The resulting solid product was washed with cold water,filtered and air-dried to give 77.6 g of the title compound with amelting point of 87°-89° C.

EXAMPLE A-2 Preparation ofN,N-dimethyl-2-chloro-5-nitrobenzenesulfonamide.

To a solution of 80 g of 2-chloro-5nitrobenzenesulfonyl chloride(Example A-1 above) in 200 ml of methylene chloride heated to reflux,was slowly added a solution of 30 g of dimethylamine hydrochloride in 30ml of water followed by a dropwise addition of triethylamine. Aftercompletion of the addition, the reaction mixture was refluxed for 20minutes, cooled to room temperature and concentrated by rotatoryevaporation. The residue was treated with water and the resulting solidwas filtered and recrystallized from ethanol, affording 61 g of thetitle compound, mp 138°-140° C.

EXAMPLE A-3

Preparation of N,N,-dimethyl-5-amino-2-chlorobenzenesulfonamide.

A mixture of 200 g of stannous chloride dihydrate and 250 ml ofconcentrated hydrochloric acid was cooled to 10° C. To the stirredmixture was added 50 g ofN,N-dimethyl-2-chloro-5-nitrobenzenesulfonamide (Example A-2 above) inportions maintaining the temperature of 10° C. After removing thecooling bath, the reaction temperature rose to 55° C. and was held fortwo hours. The reaction mixture was cooled and filtered to remove thecomplex of the product with stannic chloride. The product was treatedwith water to decompose the complex and extracted with methylenechloride. Removal of solvent from the dried extract on a rotaryevaporator gave 22 g of the title compound as a solid with a meltingpoint of 125°-126° C.

EXAMPLEA-4

Preparation of N,N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide.

50 g of N,N-dimethyl-2-chloro-5-aminobenzenesulfonamide (Example A-3above) was treated with an excess of phosgene in ethyl acetate as isgenerally described in "Organic Functional Group Preparations" by S. R.Sandler and W. Karo on pages 364-365 (Academic Press, N.Y., 1983)(preparation of organic isocyanates), which disclosure is hereinincorporated by reference. 48 g of the title compound was isolated as atan solid with a melting point of 82°-85° C.

This compound is a novel intermediate in process A and is used in thepreparation of several pyrimidinylbenzenesulfonamides of this invention.The structures of this and all previously synthesized intermediates wereconfirmed by NMR and IR spectroscopy.

EXAMPLE A-5

Preparation of N,N-dimethyl-2-chloro-5-[3,6-dihydro-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamide (Compound #5)

To 30 ml of dried tetrahydrofuran (THF) cooled to -5° C. was added,under nitrogen, 3.6 g of sodium hydride as a 60% dispersion mineral oil.To the stirred slurry was added a solution of 10 g of ethyl3-amino-4,4,4-trifluoro-2-butenoate in 30 ml of THF over a period of 30minutes. After stirring at -5° C. for 1 hour, the reaction mixture wascooled to -65° C. and a solution of N,N-dimethyl-2-chloro-5-isocyanatobenzenesulfonamide (Example A-4 above)in 30 ml of THF was added dropwise maintaining the temperature below-60° C. The mixture was stirred at -65° C. for 2 hours and allowed towarm to room temperature. After stirring for 17 hours, solvent wasremoved using a rotary evaporator. About 50 ml of water was added to theresidue. The resulting mixture was filtered to remove a small amount, ofundissolved solid and the filtrate was acidified with hydrochloric acid.The resulting precipitate was filtered to give 13 g of the titlecompound as a beige solid, m.p. 281°-283° C.

Spectral data for this compound appears in Table I.

EXAMPLE A-6

Preparation ofN,N-dimethyl-2-chloro-5-[3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H) pyrimidinyl]benzenesulfonamide (Compound #6).

A mixture of 4.0 g of compound #5 (Example A-5 above), 1.7 g of sodiumbicarbonate, 1.4 ml of dimethyl sulfate and 50 ml of acetone was heatedto reflux for 3 hours. Filtration of the solids and evaporation of thesolvent from the filtrate yielded a solid. The solid was washed withwater and was recrystallized from ethanol to give 2.5 g of the titlecompound with a melting point of 194°-196° C.

II. Preparation of[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides by processB EXAMPLE B-1

Preparation of3-(4-chloro-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione,sodium salt compound with tetrahydrofuran (1:1).

Under a blanket of nitrogen, 21.2 g of a 60% dispersion of sodiumhydride in mineral oil was washed three times with 50 ml of hexane. To astirred slurry of sodium hydride and 300 ml of dried tetrahydrofuran(THF) cooled to -10° C. was added a solution of 100 g of ethyl3-amino-4,4,4-trifluoro-2-butenoate in 400 ml of THF over a period ofone hour. The temperature was held below -5° C. during the addition. Theresulting clear brown solution was stirred an additional 15 minutes at-5° C. and then cooled to -70° C. using a Dry Ice/acetone bath. Asolution of 91.5 g of 4-chloro-2-fluorophenyl isocyanate and 200 ml ofTHF was added over one hour while maintaining the temperature between-55° C. and -70° C. The reaction mixture was allowed to slowly warm toroom temperature and was stirred at this temperature for 24 hours. Awhite solid separated and was filtered and washed with hexane to give95.5 g of the title compound as a white powder with a meltingpoint >300° C. An additional 57.2 g of the title compound was obtainedby concentrating the filtrate to 200 ml and seeding with a small amountof crystals from the first crop. The NMR spectra of both crops wereconsistent with the structure of the title compound as a 1:1 molecularaddition compound with THF.

The compound described in example B-1 is an intermediate of process B inthe synthesis of[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides. Otherexamples may be found in Table B-1 following. NMR spectroscopy was usedto confirm the structures of these compounds.

                  TABLE B-1                                                       ______________________________________                                         ##STR13##                                                                    Intermediate                                                                  Compound                                                                      #        X      Y     m    NMR(300Mhz, DMSOd.sub.6, δ)                  ______________________________________                                        A        CH.sub.3                                                                             H     1    1.75(m, 4H, CH.sub.2),                                                        2.32(s, 3H, CH.sub.3),                                                        3.60(m, 4H, CH.sub.2),                                                        5.58(s, 1H, H.sub.5),                                                         6.39(m, 2H, ArH),                                                             7.15(m, 2H, ArH)                                   B        Cl     H     1    1.75(m, 4H, CH.sub.2),                                                        3.60(m, 4H, CH.sub.2),                                                        5.61(s, 1H, H.sub.5),                                                         7.10(m, 2H, ArH),                                                             7.42(m, 2H, ArH)                                   C        Br     H     0.9  1.76(m, 3.5H, CH.sub.2),                                                      3.60(m, 3.5H, CH.sub.2),                                                      5.58(s, 1H, H.sub.5),                                                         7.05(m, 2H, ArH),                                                             7.60(m, 2H, ArH)                                   D        F      H     1    1.75(m, 4H, CH.sub.2),                                                        3.60(m, 4H, CH.sub.2),                                                        5.61(s, 1H, H.sub.5),                                                         7.15(m, 4H, ArH)                                   E        F      F     0.1.sup.a                                                                          5.61(s, 1H, H.sub.5),                                                         7.08(m, 1H, ArH)                                                              7.25(m, 2H, ArH)                                   ______________________________________                                         .sup.a Sodium salt was soluble in THF. Methylene chloride was used to         precipitate the product.                                                 

EXAMPLE B-2

Preparation of3-(4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4-(1H,3H)-pyrimidinedione.

A mixture of 130 g of the product of Example B-1, 40 ml of iodomethaneand 600ml of acetone was stirred 18 hours at room temperature and thenheated to a mild reflux for 8.5 hours. Volatiles were removed using arotary evaporator. The solid residue was then partitioned betweenmethylene chloride and water. The organic layer was washed with waterand dried with magnesium sulfate. Rotary evaporation of the solvent gavean oil which was triturated with hexane. Filtration of the resultingsolid gave 96.1 g of the title compound with a melting point of114°-116° C.

The compound described in example B-2 is an intermediate of process B inthe synthesis of[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides. Otherexamples may be found in Table B-2 following. NMR spectroscopy was usedto confirm the structures of these compounds.

                  TABLE B-2                                                       ______________________________________                                         ##STR14##                                                                    Intermediate                                                                  Compound                         NMR(300Mhz,                                  #         X       Y      MP °C.                                                                         CDCl.sub.3, δ)                         ______________________________________                                        F         CH.sub.3                                                                              H      122-124 2.39(s, 3H, CH.sub.3),                                                        3.53(d, 3H, CH.sub.3),                                                        6.35(s, 1H, H.sub.5),                                                         7.08(m, 2H, ArH),                                                             7.29(m, 2H, ArH)                             G         Cl      H      145-147 3.53(d, 3H, CH.sub.3),                                                        6.35(s, 1H, H.sub.5),                                                         7.14(m, 2H, ArH),                                                             7.46(m, 2H, ArH)                             H         F       F      89-92   3.55(d, 3H, CH.sub.3),                                                        6.36(s, 1H, H.sub.5),                                                         7.00(m, 2H, ArH),                                                             7.25(m, 1H, ArH)                             I         F       H      121-122.5                                                                             3.54(d, 3H, CH.sub.3),                                                        6.36(s, 1H, H.sub.5),                                                         7.18(d, 4H, ArH)                             J         Br      H      158.5-161                                                                             3.54(d, 3H, CH.sub.3),                                                        6.36(s, 1H, H.sub.5),                                                         7.10(m, 2H, ArH)                                                              7.63(m, 2H, ArH)                             ______________________________________                                    

EXAMPLE B-3

Preparation of2-chloro-4-fluoro-5-[(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonylchloride.

To 85 ml of chlorosulfonic acid at room temperature was added, inportions, 50 g of the product of Example B-2, with stirring. Thereaction solution was heated to 130° C. for four hours. Analysis of ahydrolyzed sample of the reaction mixture by thin layer chromatography(TLC) showed no starting material present. The mixture was cooled to 10°C. and very cautiously poured over a mixture of ice and methylenechloride. The organic layer was separated, washed with water and driedwith magnesium sulfate. The solution containing the product wasconcentrated on a rotary evaporator and diluted with hexane forming agranular slurry. The product was filtered to give 52.5 g of the titlecompound as a light tan solid, melting point 121°-125° C.

The compounds listed in Table. B-3 were prepared by thechlorosulfonation of the appropriately substituted3-phenyl-2,4(1H,3H)-pyrimidinediones as described in the example aboveand are novel intermediates to prepare the desired[3,6-dihydro-2,6-dioxo-1(2H)-pyrimidinyl]benzenesulfonamides of thisinvention by process B. The structures of these compounds were confirmedby NMR spectroscopy.

                  TABLE B-3                                                       ______________________________________                                         ##STR15##                                                                    Intermediate                                                                  Compound                          NMR(300Mhz,                                 #        R      X      Y   MP °C.                                                                        CDCl.sub.3 δ)                         ______________________________________                                        K        CH.sub.3                                                                             CH.sub.3                                                                             H   143-144                                                                              2.83(s, 3H, CH.sub.3),                                                        3.55(d, 3H, CH.sub.3),                                                        6.38(s, 1H, H.sub.5),                                                         7.49(dd, 1H, ArH.sub.4),                                                      7.54(d, 1H, ArH.sub.3)                                                        7.95(d, 1H, ArH.sub.6)                      L        H      CH.sub.3                                                                             H   226-228                                                                              (+DMSOd.sub.6)2.82(s,                                                  dec    3H, CH.sub.3),                                                                6.17(s, 1H, H.sub.5),                                                         7.57(m, 2H, ArH.sub.3,4),                                                     7.98(d, 1H, ArH.sub.6),                                                       12.6(br, 1H, NH)                            M        CH.sub.3                                                                             Cl     H   180-185                                                                              3.55(d, 3H, CH.sub.3),                                                        6.38(s, 1H, H.sub.5),                                                         7.53(dd, 1H, ArH.sub.4),                                                      7.76(d, 1H, ArH.sub.3),                                                       8.03(d, 1H, ArH.sub.6)                      N        CH.sub.3                                                                             Br     H   176-179                                                                              3.52(s, 3H, CH.sub.3),                                                        6.34(s, 1H, H.sub.5),                                                         7.42(dd, 1H, ArH.sub.4)                                                       7.95(d, 1H, ArH.sub.3),                                                       8.04(d, 1H, ArH.sub.6)                      O        CH.sub.3                                                                             F      H   179-183                                                                              3.56(s, 3H, CH.sub.3),                                                        6.39(s, 1H, H.sub.5),                                                         7.46(m, 1H, ArH),                                                             7.60(m, 1H, ArH),                                                             7.88(m, 1H, ArH.sub.6)                      P        CH.sub.3                                                                             F      F   110-113                                                                              3.58(d, 3H, CH.sub.3),                                                        6.39(s, 1H, H.sub.5)                                                          7.26(t, 1H, ArH.sub.3),                                                       7.97(m, 1H, ArH.sub.6)                      ______________________________________                                    

EXAMPLE B-4

Preparation ofN,N-diethyl-2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonamide (Compound #18).

To a solution of 1.5 ml of diethylamine and 20 ml of methylene chloridecooled to 5° C. as added, with stirring, a solution of 2.0 g of theproduct of Example B-3 and 10 ml of methylene chloride over 15 minutes.After 30 minutes the reaction mixture was poured into cold dilutesulfuric acid. The organic layer was separated and dried over magnesiumsulfate. Removal of the volatiles by rotary evaporation gave 1.9 g oftan solid. Recrystallization of the product from ethanol afforded 1.8 gof the title compound, m.p. 190°-191° C. Spectral data for this compoundis found in Table I.

EXAMPLE B-5

Preparation ofN-ethyl-2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6,-dioxo-1(2H)pyrimidinyl)benzenesulfonamide (Compound #67).

To a solution of 2.0 g of the product of Example B-3 in 30 ml ofmethylene chloride cooled to 5° C. was added 0.8 ml of a 70% solution ofethylamine in water. After stirring 1 hour at 5° C. the reaction mixturewas stirred 16 hours at room temperature. The product was isolated as asolid weighing 2.4 g following the procedure set forth in Example B-4above. Recrystallization from ethanol gave 1.7 g of the title compoundas a white crystalline solid with a melting point of 195-296° C.Spectral data for this compound is found in Table I.

EXAMPLE B-6

Preparation ofN-cyanomethyl-N-methyl-2-chloro-4-fluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide(Compound #72).

To a stirred mixture of 2.0 g of the compound of Example B-3, 0.54 g ofmethylaminoacetonitrile hydrochloride and 30 ml of methylene chloridecooled to 5° C., was added a solution of 1.4 ml of triethylamine and 10ml methylene chloride. The reaction mixture was stirred for 22 hours atroom temperature and worked up as described in Example B-4. Evaporationof solvent produced 2.2 g of a foam which crystallized from isopropanolgiving 1.8 g of the title compound as a beige solid, melting point155°-157° C. Spectral data for this compound is found in Table I.

EXAMPLE B-7

Preparation of N,N-dimethyl-2-fluoro-4-dimethylamino-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide(Compound #50).

To a solution of 2.0 g of2,4,-difluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonylchloride and 30 ml of methylene chloride cooled to 5° C. was added 1.9ml of a 40% solution of dimethylamine in water over 15 minutes. Analysisof the reaction mixture by TLC after 2 hours of stirring showed a singlecomponent. Work up was carried out as described in Example B-4. Twograms of crude solid was obtained and recrystallized from ethanol giving1.7 g of a white solid, melting point 185°-194° C. NMR analysis of theproduct showed a 2:1 mixture ofN,N-dimethyl-2,4-difluoro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide(Compound #49) and the title compound. A mixture of 1.6 g of theproduct, 30 ml of methylene chloride and 3.8 ml of a 40% solution ofdimethylamine in water was stirred at room temperature for 21 hours. Theorganic layer was separated, washed with water and dried over magnesiumsulfate. After removal of volatiles using a rotary evaporator thereremained 1.6 g of a solid. Recrystallization of the product from ethanolgave 1.4 g of the title compound as fine white crystals, m.p.223.5°-225° C. Spectral data for this compound is found in Table I.

III. Preparation of [3,6-dihydro-2,6-dioxo-1 (2H)-pyrimidinyl]benzenesulfonamides by Process C EXAMPLE C-1

Preparation ofN-(2-methoxyethyl)-N-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide(Compound #53).

To a stirred slurry of 0.2 g of a 60% dispersion of sodium hydride inmineral oil and 30 ml of N,N-dimethylformamide (DMF) cooled to 5° C. wasadded 1.95 g ofN-(2-methoxyethyl)-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide(Compound #52) prepared according to the procedure set forth aboveProcess B using2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonylchloride and 2-methoxyethylamine After stirring for 1 hour at 5° C. 0.6ml of iodomethane was added to the reaction mixture. After stirring atroom temperature for 16 hours, the mixture was concentrated using arotary evaporator. The resulting gummy residue was treated several timeswith water until a solid had formed. The solid was recrystallized fromethanol to give 1.3 g of the title compound as a white crystallinesolid, m.p. 108°-110° C. Spectral data for this compound is found inTable I.

EXAMPLE C-2

Preparation ofN-acetyl-N-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonamide(Compound #55).

To a stirred mixture of 0.≠g of a 60% dispersion of sodium hydride inmineral oil and 30 ml of DMF cooled to 5° C. was added 1.5 g ofN-methyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide. (Compound #40), prepared from2-chloropyrimidinyl)benzenesulfonyl chloride and a 40% solution ofmethylamine in water following the procedure of Process B. Afterstirring for 1 hour at 5° C., 0.75 ml of acetic anhydride was added tothe reaction mixture. After stirring at room temperature for 18 hours,the mixture was concentrated using a rotary evaporator. On treating theresidue with cold water, 1.6 g of a brown solid was obtained. Furthertreatment of the solid with boiling ethanol and filtration gave 1.25 gof the title compound as an off-white solid, m.p. 193°-195° C. Spectraldata for this compound is found in Table I.

IV. Preparation of[3,6-dihydro-2,6-dioxo-1(2H)pyrimidinyl]benzenesulfonamides by Process DEXAMPLE D-1

Preparation ofN-methyl-N-propyl-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)pyrimidinyl)benzenesulfonamide(Compound #38).

A mixture of 1.6 g of N-methyl-N-(2-propenyl)-2-chloro-5-(3,6-dihydro-3-methyl-4-trifluoromethyl-2,6-dioxo-1(2H)-pyrimidinyl)benzenesulfonamide(Compound #29), prepared by process C from Compound #28 and iodomethane,100 ml of ethyl acetate and 200 mg of 5% palladium/carbon catalyst washydrogenated in a Paar® apparatus at 28 psi of hydrogen. After 30minutes, the catalyst was filtered and solvent removed from the filtrateby rotary evaporation. The glassy residue was treated with ethanol togive 1.4 g of the title compound as a light gray powder, m.p.143.5°-145° C.

Spectral data for this compound is found in Table I. Certain compoundsdescribed in Table I exhibited non-crystalline characteristics which arenoted (when applicable) in the column designated M.P.° C. (meltingpoint). Such characteristics are designated "foam", "glass" and"resins". "Foam" may result when solvent is forced out of the productunder vacuum. "Glass" is a non-crystalline solid lacking a distinctmelting point. "Resin" is a substantially clear, semi-solid amorphoussubstance.

    TABLE I      ##STR16##       COMPOUND        PROCESS METHOD No. R R.sup.1 R.sup.2 X Y MP °C.     NMR(SOLVENT) ppm OF PREPARATION       1. H CH.sub.3 CH.sub.3 Cl Cl 288-290 (Acetoned.sub.6)2.87(s, 6H), A         6.3(s, 1H), 7.61(m, 1H),        7.78(d, 1H), 8.05(s, 1H) 2. CH.sub.3     CH.sub.3 CH.sub.3 Cl Cl 221-223 (CDCl.sub.3)2.9(s, 6H), 3.5(s,A     3H), 6.35(s, 1H), 7.7(s,        1H), 8.01(s, 1H) 3. CH.sub.2 CCH     CH.sub.3 CH.sub.3 Cl Cl 223-225 (CDCl.sub. 3)2.3(d, 2H), 2.9(s, A     6H), 4.7(s, 2H), 6.4(s, 1H),        7.8(s, 1H), 8.0(s, 1H) 4. CH.sub.2   C     CHH.sub.2 CH.sub.3 CH.sub.3 Cl Cl 171-173 (CDCl.sub.3)2.9(s, 6H), 4.5(q,     A        2H), 5.3(t, 2H), 6.0(m,        1H), 6.3(s, 1H), 7.7(s,     1H), 7.9(s, 1H) 5. H CH.sub.3 CH.sub.3 Cl H 281-283 (Acetoned.sub.6)2.85(     s, 6H), A        6.28(s, 1H), 7.65(d, 1H),        7.78(d, 1H), 8.05(s,     1H) 6. CH.sub.3 CH.sub.3 CH.sub.3 Cl H 194-196 (CDCl.sub.3)2.9(s, 6H),     3.5(s, A        3H), 6.35(s, 1H), 7.41(m,        1H), 7.6(m, 1H), 7.8(m,            1H) 7. CH.sub.2      CH.sub.3 CH.sub.3 CH.sub.3 Cl H 148-149 (CDCl.sub.3)1.36(t, 3H), 2.9(s,     A        6H), 4.02(q, 2H), 6.35(s,        1H), 7.38(m, 1H), 7.65(d,       1H), 7.95(d, 1H) 8. Na CH.sub.3 CH.sub.3 OCH.sub.3 H >250 (Dmsod.sub.6)     2.75(s, 6H), A        3.92(s, 3H), 5.62(s, 1H)        7.30(m, 3H) 9. H     CH.sub.3 CH.sub.3 OCH.sub.3 H 247-249 (Dmsod.sub.6)2.77(s, 6H), 3.96(s,     A        3H), 6.33(s, 1H), 7.37(d,        1H), 7.58(m, 1H), 7.73(d,       1H), 12.5(brs, 1H) 10. CH.sub.3 CH.sub.3 CH.sub.3 OCH.sub.3 H 168-170     (Dmsod.sub.6)2.77(s, 6H), 3.39(s, A        3H), 3.96(s, 3H), 6.48(s,        1H), 7.36(d, 1H), 7.55(m,        1H), 7.70(d, 1H) 11. CH.sub.3 H H     CH.sub.3 H 231-232 (Dmsod.sub.6)2.64(s, 3H), 3.39(s, B        3H),     6.49(s, 1H), 7.40(dd,        1H), 7.48(m, 3H), 7.78(d,        1H) 12.     CH.sub.3 CH.sub. 3 CH.sub.3 CH.sub.3 H 148-150 (CDCl.sub.3)2.67(s, 3H),     2.80(s, B        6H), 3.54(d, 3H), 6.35(s,        1H), 7.33(m, 1H),     7.45(d,        1H), 7.77(d, 1H) 13. CH.sub.3 C.sub.2 H.sub.5 C.sub.2     H.sub.5 CH.sub.3 H 156-157 (CDCl.sub.3)1.13(t, 6H), 2.65(s, B     3H), 3.32(q, 4H), 3.54(d,        3H), 6.35(s, 1H), 7.30(m,        1H),     7.41(d, 1H), 7.78(d,        1H) 14. CH.sub.3 C.sub.3 H.sub.7 -i H     CH.sub.3 H 168-169 (CDCl.sub.3)1.08(d, 6H), 2.68(s, B        3H),     3.50(m, 1H), 3.53(d,        3H), 4.62(d, 1H), 6.35(s,        1H),     7.31(m, 1H), 7.44(d,        1H), 7.88(d, 1H) 15. CH.sub.3 C.sub.4     H.sub.9 -t H CH.sub.3 H 178-180 (CDCl.sub.3)1.22(s, 9H), 2.70(s, B      3H), 3.54(s, 3H), 4.77(s,        1H), 6.35(s, 1H), 7.30(m,        1H),     7.41(d, 1H), 7.90(d,        1H) 16. CH.sub.3 CH.sub.3 CH.sub.3 Cl F     223-225 (CDCl.sub.3)2.95(s, 6H), 3.60(s, B        3H), 6.40(s, 1H),     7.46(d,        1H), 8.06(d, 1H) 17. CH.sub.3 (CH.sub.2).sub.4 CH.sub.3 H 1     80-181 (CDCl.sub.3)1.88(m, 4H), 2.69(s, B       3H), 3.31(m, 4H),     3.54(d,       3H), 6.35(s, 1H), 7.30(m,       1H), 7.44(d, 1H), 7.80(d,          1H) 18. CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 Cl F 190-191     (CDCl.sub.3)1.15(t, 6H), 3.39(q, B        4H), 3.55(d, 3H), 6.35(s,       1H), 7.42(d, 1H), 8.07(d,        1H) 19. CH.sub.3 C.sub.4 H.sub. 9 -n     C.sub.4 H.sub.9 -n Cl F 135-136 (CDCl.sub.3)0.88(t, 6H), 1.27(m, B      4H), 1.48(m, 4H)3.29(m,        4H), 3.55(d, 3H), 6.35(s,        1H),     7.40(d, 1H), 8.05(d,        1H) 20. CH.sub.3 H H Cl F 257-258 (Dmsod.sub.     6)3.41(s, 3H), 6.58(s, B        1H), 7.80(s, 2H), 7.94(d,        1H),     8.20(d, 1H) 21. CH.sub.3 CH.sub.2 CHCH.sub.2 CH.sub.2 CHCH.sub.2 Cl F     162-164 (CDCl.sub.3)3.55(d, 3H), 3.92(d, B        4H), 5.20(m, 4H),     5.68(m,        2H), 6.35(s, 1H), 7.41(d,        1H), 8.08(d, 1H) 22.     CH.sub.3 C.sub.3 H.sub.7 -n C.sub.3 H.sub.7      -n Cl F 157-158 (CDCl.sub.3)0.84(t, 6H), 1.54(m, B        4H), 3.25(m,     4H), 3.55(d,        3H), 6.35(s, 1H), 7.41(d,        1H), 8.05(d, 1H)     23. CH.sub.3 CH.sub.3 C.sub.4 H.sub.9      -n Cl F 142-143 (CDCl.sub.3)0.91(t, 3H), 1.32(m, B        2H), 1.54(m,     2H), 2.87(s,        3H), 3.22(t, 2H), 3.55(d,        3H), 6.35(s, 1H),     7.41(d,        1H), 8.04(d, 1H) 24. CH.sub.3 (CH.sub.2).sub.4 Cl F     254-255 (CDCl.sub.3)1.91(m, 4H), 3.41(m, B       4H), 3.56(d, 3H),     6.35(s,       1H), 7.43(d, 1H), 8.05(d,       1H) 25. CH.sub.3 CH.sub.3     CH.sub.2 CH.sub.2 OH Cl F 163-164 (CDCl.sub.3)2.98(s, 3H), 3.38(t, B        2H), 3.55(d, 3H), 3.70(m,        2H), 4.17(t, 1H), 6.36(s,     1H), 7.48(d, 1H), 8.07(d,        1H) 26. CH.sub.3 CH.sub.3 CH.sub.2     C.sub.6 H.sub.5 Cl F 135-136 (CDCl.sub.3)2.75(s, 3H), 3.55(d, B     3H), 4.42(m, 2H), 6.35(s,         1H), 7.31(m, 5H), 7.44(d,        1H),     8.09(d, 1H) 27. CH.sub.3 CH.sub.3 C.sub.6 H.sub.11 -c Cl F 189-190     (CDCl.sub.3)0.95-1.82(m, 10H) B        2.83(s, 3H), 3.55(d, 3H),     3.68(m, 1H), 6.35(s, 1H),        7.41(d, 1H), 8.06(d, 1H) 28. CH.sub.3 H     CH.sub.2 CHCH.sub.2 Cl H 168-170 (CDCl.sub.3)3.53(d, 3H), 3.60(m, B       2H), 5.12(m, 2H), 5.71(m,        1H), 6.35(s, 1H), 7.40(m,        2H),     7.64(d, 1H), 7.94(d,        1H) 29. CH.sub.3 CH.sub.3 CH.sub.2      CHCH.sub.2 Cl H 145-146 (CDCl.sub.3)2.83(s, 3H), 3.54(d, C        3H),     3.86(d, 2H), 5.25(m,        2H), 5.77(m, 1H), 6.35(s,        1H),     7.35(dd, 1H), 7.63(d,        1H), 7.97(d, 1H) 30. CH.sub.3 H C.sub.3     H.sub.7 -i Cl H 193-194 (CDCl.sub.3)1.10(d, 6H), 3.49(m, B        1H),     3.54(d, 3H), 4.94(d,        1H), 6.36(s, 1H), 7.37(dd,        1H),     7.64(d, 1H), 7.99(d,        1H) 31. CH.sub.3 CH.sub.3 C.sub.3 H.sub.7 -i     Cl H 172-175 (CDCl.sub.3)1.12(d, 6H), 2.82(s, C        3H), 3.54(d, 3H),     4.15(m,        1H), 6.35(s, 1H), 7.33(dd,        1H), 7.61(d, 1H),     7.98(d,        1H) 32. CH.sub.3 C.sub.2 H.sub.5 C.sub.2 H.sub.5 Cl H     181-182 (CDCl.sub.3)1.14(t, 6H), 3.39(q, B        4H), 3.54(d, 3H),     6.35(s,        1H), 7.33(dd, 1H), 7.61(d,        1H), 7.97(d, 1H) 33.     CH.sub.3 CH.sub.3 CH.sub.2 C CH Cl H 131-133 (CDCl.sub.3)2.25(t, 1H),     2.96 B        3H), 3.54(d, 3H), 4.13(d, 2H),        6.35(s, 1H),     7.36(dd,        1H), 7.63(d, 1H), 7.97(d,        1H) 34. CH.sub.3 H     C.sub.3 H.sub.5 -c Cl H 190-191 (CDCl.sub.3)0.63(m, 4H), 2.24(m, B      1H), 3.54(d, 3H), 5.43(s,        1H), 6.36(s, 1H), 7.41(dd,        1H),     7.65(d, 1H), 8.03(d,        1H) 35. CH.sub.3 CH.sub.3 C.sub.3 H.sub.5 -c     Cl H 139-141 (CDCl.sub.3)0.67(m, 4H), 2.27(m, C        1H), 2.99(s, 3H),     3.54(d,        3H), 6.34(s, 1H), 7.38(dd,        1H), 7.64(d, 1H),     8.00(d,        1H) 36. CH.sub.3 CH.sub.3 C.sub.6 H.sub.5 Cl H 170-171     (CDCl.sub.3)3.38(s, 3H), 3.51(d,B        3H), 6.31(s, 1H), 7.18-7.37(m,           6H), 7.61(d, 1H),        7.77(d, 1H) 37. CH.sub.3 H C.sub.6     H.sub.5 Cl H 225-226 (CDCl.sub.3)3.51(s, 3H), 6.33(s, B        1H),     7.10(m, 5H), 7.38(dd,        1H), 7.56(d, 1H), 8.03(d,        1H),     10.21(s, 1H) 38. CH.sub.3 CH.sub.3 C.sub.3 H.sub.7 -n Cl H 143-145     (CDCl.sub.3)0.89(t, 3H), 1.59(m, D        2H), 2.88(s, 3H), 3.22(t,       2H), 3.54(d, 3H), 6.35(s,        1H), 7.35(dd, 1H), 7.62(d,     1H), 7.95(d, 1H) 39. CH.sub.3 CH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 Cl H     glass (CDCl.sub.3)2.99(s, 3H), 3.38(s+ B        d, 8H), 3.54(d, 3H),     4.47(t,        1H), 6.36(s, 1H), 7.36(dd,        1H), 7.64(d, 1H),     7.96(d,        1H) 40. CH.sub.3 H CH.sub.3 Cl H 210-212 (CDCl.sub.3)2.64(     d, 3H), 3.54(d, B        3H), 6.36(s, 1H), 6.44(q, 1H), 7.39(dd,     1H), 7.65(d, 1H), 7.95(d,        1H) 41. CH.sub.3 CH.sub.3 CH.sub.2     CO.sub.2 C.sub.2 H.sub.5 Cl H 130-132 (CDCl.sub.3)1.24(t, 3H), 2.99(s, C            3H), 3.51(s, 3H), 4.16(s+ q,        4H), 6.35(s, 1H), 7.37(dd,         1H), 7.63(d, 1H), 7.98(d, 1H) 42. CH.sub.3 CH.sub.3 CH.sub.2     C(Cl)CH.sub.2 Cl H 138-140 (CDCl.sub.3)2.88(s, 3H), 3.55(d, C     3H), 4.10(s, 2H), 5.40(m,        1H), 5.47(m, 1H), 6.36(s,        1H),     7.38(dd, 1H), 7.65(d,        1H), 7.98(d, 1H) 43. CH.sub.3 CH.sub.3     C.sub.2 H.sub.5 Cl H 156-158 (CDCl.sub.3)1.18(t, 3H), 2.91(s, B     3H), 3.32(q, 2H), 3.55(d,        3H), 6.36(s, 1H), 7.35(dd,        1H),     7.63(d, 1H), 7.96(d,        1H) 44. CH.sub.3 CH.sub.3 CH.sub.2 CN Cl H     170-171 (CDCl.sub.3)2.98(s, 3H), 3.55(d, B        3H), 4.32(s, 2H),     6.36(s,        1H), 7.43(dd, 1H), 7.68(d, 1H),        7.98(d, 1H) 45.     CH.sub.3 CH.sub.3 OCH.sub.3 Cl H 223-234 (CDCl.sub.3)2.96(s, 3H),     3.55(d,B        3H), 3.74(s, 3H), 6.36(s,        1H), 7.44(dd, 1H),     7.69(d,        1H), 7.92(d, 1H) 46. CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2     OH Cl H 134-137 (CDCl.sub.3)2.21(bs, 1H), 3.00(s, B        3H), 3.40(t,     2H), 3.54(d,        3H), 3.73(t, 2H), 6.36(s,         1H), 7.36(dd, 1H),     7.64(d,        1H), 7.97(d, 1H) 47. CH.sub.3 CH.sub.3 CH.sub.3 F H     170-172 (CDCl.sub.3)2.85(d, 6H), 3.55(d, B        3H), 6.36(s, 1H),     7.34(t,        1H), 7.43(m, 1H), 7.75(dd,        1H) 48. CH.sub.3     CH.sub.3 CH.sub.3 Br H 205-207 (CDCl.sub.3)2.91(s, 6H), 3.55(d, B     3H), 6.36(s, 1H), 7.27(dd,        1H), 7.86(d, 1H), 7.96(d,        1H)     49. CH.sub.3 CH.sub.3 CH.sub.3 F F 205-207 (CDCl.sub.3)2.85(d, 6H),     3.56(d, B        3H), 6.36(s, 1H), 7.14(t,        1H), 7.85(t, 1H) 50.     CH.sub.3 CH.sub.3 CH.sub.3 F N(CH.sub.3).sub.2 223-225 (CDCl.sub.3)2.78(s     , 6H), 2.82(s, B        6H), 3.54(d, 3H), 6.34(s, 1H),        7.10(d,     1H), 7.60(d,        1H), 51. CH.sub.3 CH.sub.3 C.sub.4 H.sub.9 -n Cl H     140-142 (CDCl.sub.3)0.90(t, 3H), 1.32(m, B        2H), 1.55(m, 2H),     2.88(s,        3H), 3.25(t, 2H), 3.55(d,        3H), 6.36(s, 1H),     7.34(dd,        1H), 7.63(d, 1H), 7.95(d,        1H) 52. CH.sub.3 H     CH.sub.2 CH.sub.2 OCH.sub.3 Cl H 119-121 (CDCl.sub.3)3.18(m, 2H),     3.24(s,B        3H), 3.36(t, 2H), 3.55(s,        3H), 5.47(t, 1H),     6.36(s,        1H), 7.38(dd, 1H), 7.65(d,        1H), 7.97(d, 1H) 53.     CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2      OCH.sub.3 Cl H 108-110 (CDCl.sub.3)2.99(s, 3H), 3.30(s,C        3H),     3.47(t, 2H), 3.55(s+ m,        5H), 6.38(s, 1H), 7.34(dd,        1H),     7.64(d, 1H), 7.95(d,        1H)      54. CH.sub.3 CH.sub.3     ##STR17##       Cl H foam (CDCl.sub.3)2.56(m, 1H), 2.78(m,1H), 2.99(s, 3H), 3.10(m,2H),      3.55(d, 3H), 3.80(m,1H), 6.36(s, 1H), 7.38(dd,1H), 7.65(d, 1H),     7.97(d,1H) C      55. CH.sub.3 CH.sub.3 C(O)CH.sub.3 Cl H 193-195 (CDCl.sub.3)2.35(s,     3H), 3.32(s, C        3H), 3.55(s, 3H), 6.36(s,        1H), 7.45(dd,     1H), 7.66(d,        1H), 8.09(d, 1H)      56. CH.sub.3 H     ##STR18##      Cl F glass (CDCl.sub.3)1.20(td, 3H), 1.41(dd,3H), 3.55(s, 3H), 4.08(m,5.     81(m, 1H), 6.35+6.36(2s, 1H), 7.44(d, 1H),8.01(d, 1H) B  57. CH.sub.3 H      ##STR19##      Br H foam (CDCl.sub.3)3.08(m, 2H), 3.54(s,6H), 4.29(m, 1H), 5.72(d,1H),     6.35(s, 1H), 7.08-7.25(m, 6H), 7.76(d, 1H),7.91(d, 1H) B  58. CH.sub.3 H      ##STR20##       Cl F foam (CDCl.sub.3)0.92(m, 6H), 1.16(m,3H), 2.10(m, 1H), 3.55(s,     3H), 3.83(m,1H), 4.02(m, 2H), 5.67(d, 1H), 6.35(d,1H), 7.43(d, 1H),     7.97(d, 1H) B      59. CH.sub.3 H     ##STR21##      Br H foam (CDCl.sub.3)1.18(td, 3H), 2.07(s+m, 5H), 2.58(t, 2H),     3.56(s,3H), 4.10(q+m, 3H), 6.08(d,1H), 6.37(s, 1H), 7.32(dd,1H),     7.88(dd, 1H), 7.98(dd,1H) B  60. CH.sub.3 H CH.sub.2 CH.sub.2 CO.sub.2     C.sub.2 H.sub.5 Cl H glass (CDCl.sub.3)1.27(t, 3H), 2.53(t, B     2H), 3.25(q, 2H), 3.56(s,        3H), 4.16(q, 2H), 5.89(t,        1H),     6.37(s, 1H), 7.43(m,        1H), 7.66(d, 1H), 7.99(d,        1H) 61. H     CH.sub.3 CH.sub.3 CH.sub.3 H 310 dec (Dmsod.sub.6)2.60(s, 3H), 2.73(s, B            6H), 6.33(s, 1H), 7.52(m,        2H), 7.75(s, 1H), 12.5(brs,       1H) 62. H H C.sub.2 H.sub.5 CH.sub.3 H 240-242 (Dmsod.sub.6)0.99(t,     3H), 2.62(S, B        3H), 2.85(m, 2H), 6.32(s,        1H), 7.47(m, 2H),     7.70(t,        1H), 7.78(s, 1H), 12.5(s,        1H) 63. H CH.sub.3     C.sub.2 H.sub.5 CH.sub.3 H 247-250 (Dmsod.sub.6)1.09(t, 3H), 2.58(s, B          3H), 2.77(s, 3H), 3.19(q,        2H), 6.33(s, 1H), 7.50(m,     2H), 7.75(s, 1H), 12.5(s, 1H) 64. H H C.sub.3 H.sub.7 -i CH.sub.3 H     217-220 (Dmsod.sub.6)0.98(d, 6H), 2.62(s, B        3H), 3.27(m, 1H),     6.32(s,        1H), 7.46(m, 2H), 7.68(d,        1H), 7.81(s, 1H),     12.5(s,        1H) 65. H H CH.sub.2 CH.sub.2 OCH.sub.3 CH.sub.3 H     238-240 (Dmsod.sub.6 )2.61(s, 3H), 2.97(q, B        2H), 3.11(s, 3H),     3.28(t,        2H), 6.32(s, 1H), 7.47(m,        2H), 7.78(d, 1H),     7.85(t,        1H) 12.5(s, 1H) 66. CH.sub.3 CH.sub.3 C.sub.2 H.sub.5 Cl     F 190-191 (CDCl.sub.3)1.18(t, 3H), 2.90(s, B        3H), 3.31(q, 2H),     3.56(d,        3H), 6.36(s, 1H), 7.42(d, 1H),        8.04(d, 1H) 67.     CH.sub.3 H C.sub.2 H.sub.5 Cl F 195-196 (CDCl.sub.3)1.11(t, 3H), 3.00(m,     B        2H), 3.55(s, 3H), 6.37(s,        1H), 7.17(t, 1H), 7.46(d,       1H), 8.06(d, 1H) 68. CH.sub.3 H CH.sub.3 Cl F 187-189 (CDCl.sub.3)2.62(     d, 3H), 3.55(s, B        3H), 6.37(s, 1H), 7.08(d,        1H), 7.47(d,     1H), 8.05(d,        1H) 69. CH.sub.3 CH.sub.3 CH.sub. 2 CCH Cl F 178-179     (CDCl.sub.3)2.26(t, 1H), 2.97(s, B        3H), 3.56(d, 3H), 4.12(d,       2H), 6.36(s, 1H), 7.43(d,        1H), 8.05(d, 1H) 70. CH.sub.3 H     C.sub.3 H.sub.5 -c Cl F 187-190 (CDCl.sub.3)0.50(m, 4H), 2.27(m, B      1H), 3.52(s, 3H), 6.41(s,        1H), 7.62(d, 1H), 8.18(d+s,        2H)     71. CH.sub.3 CH.sub.3 CH.sub.2      CH(OCH.sub.3).sub.2 Cl F glass (CDCl.sub.3)2.99(s, 3H), 3.38(s+ B      m, 8H), 3.56(d, 3H), 4.47(t,        1H), 6.36(s, 1H), 7.44(d,     1H), 8.02(d, 1H) 72. CH.sub.3 CH.sub.3 CH.sub.2      CN Cl F 155-157 (CDCl.sub.3)2.98(s, 3H), 3.56(d, B        3H), 4.32(s,     2H), 6.37(s,        1H), 7.48(d, 1H), 8.07(d,        1H) 73. CH.sub.3     CH.sub.3 OCH.sub.3 Cl F 167-169 (CDCl.sub.3)2.94(s, 3H), 3.56(d, B      3H), 3.74(s, 3H), 6.36(s,        1H), 7.48(d, 1H), 8.00(d,        1H)     74. CH.sub.3 H CH.sub.2 CH.sub.2      OCH.sub.3 Cl F 170-172 (CDCl.sub.3)3.17(m, 2H), 3.25(s, B        3H),     3.37(t, 2H), 3.56(s,        3H), 5.48(t, 1H), 6.36(s,        1H),     7.45(d, 1H), 8.05(d,        1H) 75. CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2     OCH.sub.3 Cl F oil (CDCl.sub.3)3.00(s, 3H), 3.31(s, C        3H),     3.48(m, 2H), 3.55(m,        5H), 6.37(s, 1H), 7.45(d,        1H),     8.06(d, 1H) 76. CH.sub.3 CH.sub.2 CH.sub.2 OCH.sub.2 CH.sub.2 Cl F     203-204 (CDCl.sub.3)3.29(t, 4H), 3.56(s, B       3H), 3.73(t, 4H),     6.36(s,       1H), 7.45(d, 1H), 8.02(d,       1H) 77. CH.sub.3 CH.sub.2     CH.sub.2 OH CH.sub.2 CH.sub.2 OH Cl F 160-164 (CDCl.sub.3)3.48, 3.55,     3.62(t+ B        s+brs, 9H), 3.78(t, 4H),        6.36(s, 1H), 7.44(d,     1H), 8.06(d,        1H) 78. CH.sub.3 CH.sub.3 CH.sub.2 CH.sub.2 CN Cl F     foam (CDCl.sub.3)2.69(t, 2H), 3.00(s, 3H),        3.56(d, 3H), 3.60(t,     2H), 6.36(s,        1H), 7.46(d, 1H), 8.05(d, 1H)  79. CH.sub.3 CH.sub.3      ##STR22##      Cl F foam (CDCl.sub.3)3.00(s, 3H), 3.47(t, 2H),3.56(d, 3H), 3.88(m,     4H), 5.04(t,1H), 6.36(s, 1H), 7.42(d, 1H),8.05(d, 1H)  80. CH.sub.3 H     CH.sub.2 CH(OCH.sub.3).sub.2 Cl F foam (CDCl.sub.3)3.13(t, 2H), 3.30(d,     6H), 3.56(d,        3H), 4.25(t, 1H), 5.33(t, 1H), 6.36(s,        1H),     7.45(d, 1H), 8.03(d, 1H) 81. CH.sub.3 CH.sub.3 CH.sub.2      CH(OCH.sub.3).sub.2 Br H foam (CDCl.sub.3)2.98(s, 3H), 3.39(s+m, 8H),          3.55(d, 3H), 4.47(t, 1H), 6.36(s, 1H),        7.28(dd, 1H), 7.86(d,     1H), 7.97(d, 1H) 82. CH.sub.3 CH.sub.3 CH.sub.2 CH(OCH.sub.3).sub.2 F H     resin (CDCl.sub.3)2.99(d, 3H), 3.30(d, 2H), 3.39(s,        6H), 3.56(d,     3H), 4.49(t, 1H), 6.37(s,        1H), 7.30-7.48(m, 2H), 7.79(dd, 1H)     83. CH.sub.3 CH.sub.3      ##STR23##      Br H foam (CDCl.sub.3)2.99(s, 3H), 3.50(d, 2H),3.54(d, 3H), 3.90(m,     4H), 5.06(t,1H), 6.35(s, 1H), 7.26(dd, 1H),7.99(d, 1H)  84. CH.sub.3     CH.sub.3 CH.sub.2 CHO Cl F foam (CDCl.sub.3)2.96(s, 3H), 3.56(d, 3H),         4.17(s, 2H), 6.37(s, 1H), 7.46(d, 1H),        8.06(d, 1H), 9.64(s,     1H) 85. CH.sub.3 CH.sub.3 CH.sub.2      CH(OCH.sub.3).sub.2 F Fresin (CDCl.sub.3)2.99(d, 3H), 3.29(dd, 2H),        3.39(d, 6H), 3.57(d, 3H), 4.49(t, 1H),        6.37(s, 1H), 7.15(t,     1H), 7.87(t, 1H)

V. Preemergence Control

To illustrate the effectiveness of the compounds of this invention aspreemergence herbicides, 300 mg of each of the below listed compoundswere dissolved in 10 ml acetone to which 30 mg of an emulsifying agent,ethoxylated sorbitan monolaurate, were added. The solution was dilutedto 100 ml with distilled water. Ten milliliters of the 3000 ppm solutionwere diluted to 250 ppm with distilled water. The chemical was appliedat the rate of 10 lb/A (11.2 kg/ha) by drenching 46 ml of the 250 ppmsolution on the surface of soil in 41/2 inch (11.25 cm) plastic potswherein seeds of the following weeds had been planted: Prickly sida(Sida spinosa L.) (PS), jimsonweed (Datura stramonium L. (JW), tallmorningglory (Ipomea purpurea L. Roth) (TM), switchgrass (Panicumvirgatum L.) (SG), barnyardgrass (Echinochloa crusgalli L. Beauv.) (BG),and green foxtail (Setaria viridis (L.), Beauv.) (GF). The percentcontrol of the weeds compared to untreated checks was determined twoweeks after treatment. The results of such testing are summarized inTable II. The data presented in such table indicated the good toexcellent herbicidal efficacy of the compounds of this invention.

                  TABLE II                                                        ______________________________________                                        Preemergence Activity of 10 lb/A (11.2 kg/ha)                                 Percent Weed Control at 11.2 kg/ha                                            Com-                                                                          pound                                                                         #     VL     JW      PS    TM    SG    BG    GF                               ______________________________________                                         1    0      0       --    0     35    50    20                                2    100    100     --    100   95    90    100                               3    0      0       --    0     0     0     0                                 4    0      0       --    0     0     0     0                                 5    0      0       --    50    75    0     65                                6    100    100     --    100   100   100   100                               7    100    100     --    100   100   95    100                               8    0      0       --    0     0     0     0                                 9    0      0       --    0     0     0     0                                10    100    0       --    100   0     0     90                               11    100    50      --    100   100   0     95                               12    100    100     --    100   100   100   100                              13    100    100     --    100   100   100   100                              14    100    40      --    95    65    0     100                              15    100    95      --    100   100   100   100                              16    100    --      --    95    100   100   100                              17    100    --      100   100   100   60    100                              18    100    --      100   100   100   100   100                              19    100    --      100   25    100   35    100                              20    100    --      100   100   100   95    100                              21    100    --      100   90    100   95    100                              22    100    --      100   100   100   100   100                              23    95     --      100   0     100   --    95                               24    100    --      100   90    100   --    50                               25    100    --      100   100   100   --    100                              26    100    --      100   100   100   --    100                              27    95     --      100   25    100   --    100                              28    100    --      100   100   100   20    100                              29    100    --      100   100   100   100   100                              30    100    --      100   100   100   45    100                              31    100    --      100   100   100   90    100                              32    100    --      100   100   90    95    100                              33    100    --      100   100   90    100   100                              34    100    --      100   100   100   100   100                              35    100    --      100   100   100   100   100                              36    100    --      100   0     0     20    0                                37    0      --      0     0     0     0     50                               38    100    --      100   95    100   40    75                               39    100    --      100   100   100   100   100                              40    100    --      100   100   100   60    100                              41    100    --      100   100   100   100   100                              42    100    --      100   95    100   90    100                              43    100    --      100   100   100   100   100                              44    100    --      100   100   100   100   100                              45    100    --      100   100   100   100   100                              46    100    --      100   100   100   100   100                              47    100    --      100   100   100   100   100                              48    100    --      100   100   100   100   100                              49    100    --      100   100   100   100   100                              50    100    --      100   0     100   0     95                               51    0      --      0     80    20    50    95                               52    100    --      100   100   100   100   100                              53    100    --      100   95    100   100   100                              54    100    --      100   100   100   100   100                              55    100    --      100   100   100   100   100                              56    100    --      100   100   100   100   100                              57    100    --      100   100   100   95    100                              58    100    --      100   100   100   100   100                              59    85     --      100   100   100   0     100                              60    100    --      100   100   100   0     100                              61    0      --      0     0     0     0     0                                62    0      --      100   0     0     60    100                              63    0      --      0     0     100   0     50                               64    90     --      100   100   95    90    100                              65    0      --      0     0     0     0     50                               66    100    --      100   100   100   100   100                              67    100    --      100   100   100   100   100                              68    100    --      100   100   100   100   100                              69    100    --      100   80    100   80    100                              70    100    --      100   100   100   100   100                              71    100    --      100   100   100   100   100                              72    100    --      100   100   100   100   100                              73    100    --      100   90    100   100   100                              74    100    --      100   100   100   100   100                              75    100    --      100   100   100   100   100                              76    100    --      100   100   100   100   100                              77    100    --      100   100   100   100   100                              78    100    100     100   100   100   100   100                              79    100    100     100   100   100   100   100                              80    100    100     100   90    100   100   100                              81    100    100     100   100   100   100   100                              82    100    100     100   90    90    95    100                              83    100    100     100   100   100   100   100                              84    100    100     100   100   100   100   100                              85    100    100     100   100   100   100   100                              ______________________________________                                    

VI. Postemergence Control

To test the effectiveness of the compounds of this invention aspostemergence herbicides, the 3000 ppm solution described in Example V(Preemergence Control) was atomized employing a DeVILBISS™ sprayer,wetting the foliage to the drip point. The remainder of the procedurewas the same as described in Example 4. The weeds, which were the samespecies as described in Example V, were treated six days afteremergence. The percent weed control was evaluated two weeks aftertreatment. The results of such testing are summarized in Table III.

                  TABLE III                                                       ______________________________________                                        Postemergence Herbicide Activity of 3000 ppm                                  Percent Weed Control at 11.2 kg/ha                                            Com-                                                                          pound                                                                         #     VL     JW      PS    TM    SG    BG    GF                               ______________________________________                                              75     15      --    50    0     10    5                                 2    100    100     --    95    75    90    80                                3    100    100     --    100   100   100   100                               4    20     0       --    30    20    75    65                                5    15     10      --    15    0     5     0                                 6    100    100     --    100   45    80    95                                7    100    100     --    100   20    55    50                                8    0      0       --    0     0     0     0                                 9    0      0       --    0     0     0     0                                10    50     30      --    55    0     5     5                                11    95     95      --    100   0     25    10                               12    100    100     --    100   25    60    45                               13    100    95      --    100   10    70    55                               14    80     50      --    70    35    0     25                               15    95     50      --    95    5     5     10                               16    100    100     --    100   100   100   100                              17    100    --      --    100   75    80    95                               18    100    --      --    90    100   90    100                              19    95     --      --    40    30    45    35                               20    100    --      80    100   70    65    45                               21    100    --      90    100   95    85    85                               22    100    --      100   100   95    70    85                               23    100    --      100   100   75    100   85                               24    100    --      90    100   80    80    45                               25    100    --      100   100   40    75    45                               26    100    --      95    100   40    75    65                               27    100    --      90    100   35    60    20                               28    100    --      100   75    50    85    20                               29    100    --      100   100   10    75    55                               30    100    --      100   100   15    40    25                               31    100    --      100   85    30    70    15                               32    100    --      100   70    60    75    100                              33    100    --      100   95    95    80    100                              34    100    --      95    100   30    40    95                               35    100    --      100   100   75    80    50                               36    100    --      30    15    5     20    25                               37    65     --      40    10    0     15    20                               38    100    --      100   95    20    45    15                               39    100    --      100   100   100   100   100                              40    100    --      100   100   90    35    80                               41    100    --      100   100   100   95    90                               42    100    --      100   60    40    50    30                               43    100    --      100   100   100   90    85                               44    100    --      100   95    55    70    45                               45    100    --      100   90    10    45    55                               46    100    --      100   100   5     70    95                               47    95     --      95    90    10    15    100                              48    100    --      100   100   100   90    100                              49    100    --      100   100   100   75    100                              50    95     --      90    40    0     0     0                                51    100    --      100   95    10    30    20                               52    100    --      100   100   100   50    100                              53    100    --      100   100   100   95    100                              54    100    --      100   100   100   100   100                              55    100    --      100   95    20    90    65                               56    100    --      100   100   100   100   100                              57    100    --      100   100   100   60    70                               58    100    --      100   100   100   100   95                               59    95     --      95    65    0     0     0                                60    100    --      100   100   95    95    90                               61    15     --      0     0     0     0     0                                62    15     --      10    20    0     0     0                                63    10     --      5     10    15    0     0                                64    25     --      50    10    10    0     75                               65    0      --      0     0     0     0     0                                66    100    --      100   100   90    75    85                               67    100    --      100   100   100   100   100                              68    100    --      100   100   100   95    100                              69    100    --      100   100   85    65    80                               70    100    --      100   100   90    90    95                               71    100    --      100   100   100   100   100                              72    100    --      100   100   100   100   100                              73    100    --      100   100   100   100   100                              74    100    --      100   100   90    75    95                               75    100    --      100   100   100   100   100                              76    100    --      100   100   100   95    100                              77    100    --      100   100   100   100   100                              78    100    100     100   100   100   100   95                               79    100    100     100   100   100   100   100                              80    100    100     100   100   80    70    80                               81    100    100     100   100   65    95    90                               82    100    100     100   60    20    35    15                               83    100    100     100   100   100   100   90                               84    100    100     100   100   100   100   100                              85    100    100     100   100   100   90    65                               ______________________________________                                    

What is claimed is:
 1. An isocyanatobenzenesulfonamide compound of thestructural formula ##STR24## wherein X is C₁ -C₄ alkyl, C₁ -C₈ alkoxy orhalogen;Y is hydrogen, halogen, or C₁ -C₄ dialkylamino; R¹ is C₁ -C₈straight chain or branched alkyl, C₃ -C₈ cycloalkyl, C₃ -C₈ alkenyl orC₃ -C₈ alkoxy; R² is C₁ -C₈ straight chain or branched alkyl, C₃ -C₈alkenyl, C₃ -C₈ cycloalkyl, halo substituted C₃ -C₈ alkenyl, C₃ -C₈alkynyl, C₁ -C₄ alkoxy, cyano C₁ -C₄ alkyl, alkoxyalkyl, phenyl,aralkyl, C₁ -C₄ acyl, C₁ -C₄ carbalkoxyalkyl, C₁ -C₄ phenyl, aralkyl, C₁-C₄ acyl, C₁ -C₄ carbalkoxyalkyl, C₁ -C₄ carbalkoxyalkyl substituted byC₁ -C₄ alkyl, phenylmethyl or methylthioethyl, dialkylaminoethyl, ortetrahydrofuranylmethyl; R¹ and R² taken together form a C₃ -C₈ memberedheterocyclic ring containing one or more heteroatoms.